Originally, the producers were looking for a Latina or Asian Tracy Flick but could not find any. For the role of Annie, Harmon wanted someone who would resemble Tracy Flick, Reese Witherspoon's character from the 1999 movie Election. was so head and shoulders above everything else that I was reading." McHale appealed to Harmon because of his likeable quality, which allowed the character to possess certain unsympathetic traits without turning the viewer against him. McHale, known from the E! comedy talk show The Soup, was also (like Chase) impressed by Harmon's writing. Though Chase has often been ridiculed for his career choices, Harmon believed this role could be redeeming: "What makes Chevy and Pierce heroic is this refusal to stop." Harmon had to warn Chase against playing a "wise-ass" the way he often does in his roles, since the character of Pierce is a rather pathetic figure who is normally the butt of the joke himself. Harmon saw similarities between Chase and the character he plays on the show. Though principally not very partial to sitcoms, Chase was persuaded to take the job by the quality of the show's writing. Actor Chevy Chase had long been a favorite of Harmon.
He had worked with several of the cast members earlier Joel McHale, John Oliver, and Chevy Chase all had cameo roles in Episode 9 of Water and Power, the short film series produced by Harmon for Channel 101. "Casting was 95 percent of putting the show together," he said in an interview.
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